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Two Week Amalfi Coast & Greece Trip - Help Please

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My husband and I (early 30's) are planning a trip end of July to the Amalfi coast and a couple Greek islands for two weeks. 7 in Italy and 7 in the Greek Isles. Here is our itinerery so far. Let me know what you think of the hotels I've picked and if we should rent a car from Naples to Sorrento or get a driver. My travel agent is quoting us for private transfers and the price seems really steep.
July 21 - Naples (1 night) Transfer to hotel Hotel Piazza Bellini (is it hard to take the train into Naples on our own or should we get a private transfer?)
-Tour city on our own
July 22 -En route to Sorrento (not sure how much is it for a driver, without the tour to Pompeii and Herculaneum. Thought about taking the Circumvesuviana train to Herculaneum - (is it worth it to go here?) and then Pompeii,but then we'll have all of our luggages with us. So I don't think that's a good idea.

In Sorrento,(1 night - is that enough? our goal is to get to capri and Positano/Amalfi) we're thinking of staying at either:
1) Hotel Mediterraneo - seaview room (seems a little far from city centre though)
2) Antiche Mura Hotel
Is it hard to get to the marina on our own in Sorrento? Should we stay in the town or in a little place called Sant. Agnello?

July 23 -Ferry to Capri - (1 night) see Grotto, tour the town, maybe some hiking - where is a good place to hike? Should we bother with the little boat going into the Blue Grotto? I heard in the summer you have to wait about 3 hours just to get in for a 10 minute ride!
-Overnight in Capri at La Minerva
July 24 - Hydrofoil to Amalfi or Positano (2 nights) (which should we stay at? Positano or Amalfi? some of my coworkers said they liked Amalfi more)
-Transfer to hotel
- Enjoy Amalfi and day trip to Ravello (should we rent a car from here or do tours)
July 25 -Day trip to Positano
July 26 -Transfer back to Naples in afternoon
-overnight in Naples hotel Hotel Piazza Bellini
July 27 -fly to Athens and go directly to pier(how difficult is it to get from airport to the pier?) to take jetfoil to Mykonos (2 nights). In Mykonos we're thinking of staying at:
1) Petsos Beach Resort and Spa
2) Mykonos Grand
July 28 -Hydrofoil to Santorini (2 nights) - haven't decided where to stay yet. Want something that overlooks the sea. Everything is so expensive!!!
July 30 - transfer back to Naples and fly out to Paris for a few nights!! woohoo!

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